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2-methoxythiophene

2-methoxythiophene is a sulfur-containing heterocyclic compound with a methoxy group at the 2-position, noted for its mustard-like flavor.
Chemical Structure

General Material Description

2-methoxythiophene is an organic compound characterized by a five-membered sulfur heterocycle (thiophene) bearing a methoxy substituent at the 2-position. It is a volatile liquid with the molecular formula C5H6OS and a molecular weight of approximately 114.17 g/mol. This compound exhibits a distinctive mustard-like flavor profile, although it is primarily used for informational and research purposes rather than in commercial flavor or fragrance formulations. Known synonyms include methyl 2-thienyl ether and thienyl methyl ether. Its structure and data are catalogued in authoritative repositories such as PubChem. The compound can be sourced synthetically via typical heterocyclic ether formation methodologies and is noted for its distinct chemical and physical properties.

Occurrence, Applicability & Potential Uses

2-methoxythiophene does not naturally occur in significant biological systems but belongs to the class of sulfur-containing heterocycles often studied for chemical and analytical interest. Its primary application is informational; it is not utilized in food flavoring or fragrance products. Regulatory acknowledgment such as REACH (EU) addresses its chemical registration rather than its use in consumer products. Research involving 2-methoxythiophene may relate to its physicochemical behavior or as a chemical intermediate in heterocyclic synthesis but commercial uses are minimal. Due to insufficient safety usage data, professional guidelines recommend omitting its use in fragrances and flavors.

Physico-Chemical Properties Summary

2-methoxythiophene exhibits key properties influencing its handling and potential formulation impacts. It has a moderate molecular weight (114.17 g/mol) and a log P value near 2.13, indicating moderate lipophilicity. The compound boils between 147 and 148 °C at atmospheric pressure, with a vapor pressure of roughly 5.57 mmHg at 25 °C, suggesting moderate volatility. Its specific gravity ranges from 1.136 to 1.141 at 20 °C, and refractive indices fall between 1.526 and 1.529 at 20 °C. Solubility data indicate it is soluble in alcohol and slightly soluble in water, with estimated water solubility around 1597 mg/L at room temperature. The flash point stands at 110 °F (approximately 43 °C), which has implications for safety in handling and storage. These properties affect its behavior in mixtures and suitability for various chemical applications.

FAQ

What is 2-methoxythiophene and how is it characterized?
2-methoxythiophene is an organic heterocyclic compound containing a thiophene ring substituted with a methoxy group at the 2-position. It is identified by the molecular formula C5H6OS and exhibits a distinctive mustard-like flavor note. This compound is a volatile liquid with moderate boiling point and lipophilicity, catalogued under CAS number 16839-97-7. It is primarily studied as a chemical entity rather than used commercially in flavors or fragrances. Its synonyms include methyl 2-thienyl ether and thienyl methyl ether.
Where does 2-methoxythiophene occur and what are its typical applications?
2-methoxythiophene is not commonly found in nature but belongs to sulfur heterocycles of interest in chemical research. It is not currently used in flavors or fragrances and its applications are mainly limited to informational or experimental settings. Regulatory frameworks such as REACH (EU) focus on its safety registration rather than product application. The compound may serve as a chemical intermediate in synthesis, but direct commercial uses are minimal due to insufficient safety data for consumer products.
How is 2-methoxythiophene regulated and where can reliable safety information be found?
2-methoxythiophene is subject to chemical registration and safety assessments under regulations including REACH in the European Union. No established usage levels are recommended for fragrances or flavors, reflecting its informational use status. Safety data sheets and toxicological reports are available from sources such as the EPA, PubChem, and the National Institute of Allergy and Infectious Diseases. These repositories provide chemical hazard classifications and physicochemical data but do not include exposure limits or approved uses in consumer products.

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2934.99.9000
ChemSpider:View

General Material Information

Preferred name 2-methoxythiophene
Trivial Name 2-Methoxythiophene
Short Description thiophene, 2-methoxy
Formula C5 H6 O S
CAS Number 16839-97-7
ECHA Number 240-863-2
FDA UNII Search
Nikkaji Number J151.062B
MDL MFCD00014526
xLogP3-AA 1.90 (est)
NMR Predictor External link
Synonyms
  • 2-methxoythiophene
  • methyl 2-thienyl ether
  • thienyl methyl ether
  • thiophene, 2-methoxy
  • thiophene, 2-methoxy-

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 114.16702270508
Specific gravity @ 20 °C
Pounds per Gallon 9.464 to 9.505
Refractive Index 1.526 to 1.529 @ 20 °C
Boiling Point 147 to 148°C @ 760 mm Hg
Vapor Pressure 5.57 mmHg @ 25 °C
Flash Point TCC Value 43.33 °C TCC
logP (o/w) 2.13
Solubility
alcohol Yes
water, 1597 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Flavor Type: Mustard
mustard
General comment Mustard

Safety Information

Safety information

Preferred SDS: View
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in use information

Category:
information only not used for fragrances or flavors
Recommendation for 2-methoxythiophene usage levels up to:
not for fragrance use.
Recommendation for 2-methoxythiophene flavor usage levels up to:
not for flavor use.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :85610
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-methoxythiophene
Chemidplus:0016839977